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$120+ Cheap flights from Midland (MAF) to Caribbean

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/13. Fares are subject to change and may not be available on all flights or dates of travel.
MAF — SJU
Jan 7 — Jan 141
Wed 1/7
Wed 1/14
1 adult, Economy
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Cheap flight deals from Midland to Caribbean

Cheapest flights from Midland to Caribbean
Explore the most affordable flight options available from Midland to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 8, 2025.

This Southwest deal was found by Cheapflights users on 12/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/135:50 amMAF - SJU
2 stops9h 25mSouthwest
Sat 12/203:35 pmSJU - MAF
2 stops10h 35mSouthwest
Deal found 12/6$502
This United Airlines deal was found by Cheapflights users on 12/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/147:00 amMAF - SJU
1 stop7h 36mUnited Airlines
Wed 12/173:46 pmSJU - MAF
1 stop9h 27mUnited Airlines
Deal found 12/6$519
This American Airlines deal was found by Cheapflights users on 12/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/148:27 pmMAF - SJU
1 stop6h 52mAmerican Airlines
Wed 12/1711:00 amSJU - MAF
2 stops11h 23mAmerican Airlines
Deal found 12/7$575
This American Airlines deal was found by Cheapflights users on 12/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/218:28 pmMAF - SJU
1 stop16h 45mAmerican Airlines
Thu 12/256:57 pmSJU - MAF
2 stops16h 52mAmerican Airlines
Deal found 12/7$755
This American Airlines deal was found by Cheapflights users on 12/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/228:28 pmMAF - SDQ
2 stops17h 21mAmerican Airlines
Sun 12/284:49 pmSDQ - MAF
2 stops17h 52mAmerican Airlines
Deal found 12/7$807
This American Airlines deal was found by Cheapflights users on 12/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:00 amMAF - SDQ
2 stops33h 56mAmerican Airlines
Tue 12/306:00 amSDQ - MAF
2 stops13h 34mAmerican Airlines
Deal found 12/7$919
This American Airlines deal was found by Cheapflights users on 12/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2410:19 amMAF - SDQ
2 stops29h 37mAmerican Airlines
Mon 12/296:57 pmSDQ - MAF
2 stops24h 37mAmerican Airlines
Deal found 12/7$924
This American Airlines deal was found by Cheapflights users on 12/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/247:35 amMAF - SDQ
2 stops30h 16mAmerican Airlines
Sun 12/286:57 pmSDQ - MAF
2 stops15h 44mAmerican Airlines
Deal found 12/7$929
This deal was found by Cheapflights users on 12/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/227:00 amMAF - SJU
1 stop7h 36mUnited Airlines
Thu 12/257:45 amSJU - MAF
1 stop9h 19mUnited Airlines
Deal found 12/6$930
This American Airlines deal was found by Cheapflights users on 12/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2310:19 amMAF - SDQ
2 stops25h 57mAmerican Airlines
Tue 12/304:49 pmSDQ - MAF
2 stops19h 00mAmerican Airlines
Deal found 12/7$947
This American Airlines deal was found by Cheapflights users on 12/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:00 amMAF - SDQ
2 stops33h 56mAmerican Airlines
Sat 12/276:57 pmSDQ - MAF
2 stops29h 40mAmerican Airlines
Deal found 12/7$950
This American Airlines deal was found by Cheapflights users on 12/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2310:19 amMAF - SDQ
2 stops27h 30mAmerican Airlines
Mon 12/296:57 pmSDQ - MAF
2 stops27h 01mAmerican Airlines
Deal found 12/7$952

Find flight deals from Midland to Caribbean

Keep the following information in mind while searching for Midland to Caribbean flight deals. Data was last updated December 8, 2025.

Round-trip from

$415
(United Airlines)

One-way from

$120
(United Airlines)

Popular in

February

Cheapest in

April

Average price

$731
From Midland Intl to Caribbean
Search Deals
One-way flight from Midland Intl to Caribbean
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($58 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($23 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Midland to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 8, 2025.
Use the filters below to find and compare flights from Midland to Caribbean that are best for you.

Fly from

Midland

Fly to

Caribbean

Route

Depart

Return

Price

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Tue 1/6

7:00 am-4:36 pm

1 stop7h 36m

San Juan Luis Munoz Marin Intl

Tue 1/13

3:46 pm-9:54 pm

1 stop8h 08m

$415

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Tue 1/6

6:40 am-7:05 pm

2 stops10h 25m

San Juan Luis Munoz Marin Intl

Tue 1/13

5:40 am-2:10 pm

2 stops10h 30m

$443

MidlandMontego Bay

MAF - MBJ

MAFMBJ

Midland Intl

Sun 3/15

6:20 pm-11:24 am

2 stops17h 04m

Montego Bay Sangster Intl

Wed 3/25

3:04 pm-12:06 am

1 stop9h 02m

$480

MidlandSanto Domingo

MAF - SDQ

MAFSDQ

Midland Intl

Sat 1/17

1:45 pm-1:41 pm

2 stops21h 56m

Santo Domingo Las Americas

Wed 1/21

6:00 am-9:54 pm

2 stops17h 54m

$642

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Sun 12/21

8:28 pm-3:13 pm

1 stop16h 45m

San Juan Luis Munoz Marin Intl

Thu 12/25

6:57 pm-9:49 am

2 stops16h 52m

$755

MidlandSanto Domingo

MAF - SDQ

MAFSDQ

Midland Intl

Wed 12/24

10:19 am-5:56 pm

2 stops29h 37m

Santo Domingo Las Americas

Mon 12/29

6:57 pm-5:34 pm

2 stops24h 37m

$924

MidlandSanto Domingo

MAF - SDQ

MAFSDQ

Midland Intl

Wed 12/24

7:35 am-3:51 pm

2 stops30h 16m

Santo Domingo Las Americas

Sun 12/28

6:57 pm-8:41 am

2 stops15h 44m

$929

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Mon 12/22

7:00 am-4:36 pm

1 stop7h 36m

San Juan Luis Munoz Marin Intl

Thu 12/25

7:45 am-3:04 pm

1 stop9h 19m

$930

MidlandSanto Domingo

MAF - SDQ

MAFSDQ

Midland Intl

Tue 12/23

10:19 am-3:49 pm

2 stops27h 30m

Santo Domingo Las Americas

Fri 12/26

3:16 pm-8:41 am

2 stops19h 25m

$947

MidlandSanto Domingo

MAF - SDQ

MAFSDQ

Midland Intl

Tue 12/23

10:19 am-2:16 pm

2 stops25h 57m

Santo Domingo Las Americas

Thu 12/25

3:16 pm-8:41 am

2 stops19h 25m

$947

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/6

Showing 1-10 of 23 results
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Best time to book a flight from Midland to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Midland with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Midland to Caribbean

What is the cheapest month to book a flight from Midland to Caribbean?

Currently, April is the cheapest month in which you can book a flight from Midland to Caribbean (average of $247). Flying from Midland to Caribbean in July is currently the most expensive (average of $666). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MAF to CB?

Find hourly flight availability from Midland to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 8, 2025.

It’s typically best to fly out from Midland to Caribbean in the evening. Doing so could potentially save you 23% on the flight price compared to flying at noon, which is usually more expensive.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated December 8, 2025.
Read through reviews of airlines operating flights from Midland to Caribbean, such as Southwest, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,252 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,252 reviews
Southwest
8.0
Very good
4,252 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,076 reviews
Southwest
8.0
Very good
4,252 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,042 reviews
Southwest
8.0
Very good
4,252 reviews

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Midland to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Midland to Caribbean?

    Most people fly from Midland Intl (MAF) if they book a flight from Midland to Caribbean. Midland Intl is conveniently located just 8.2 mi from Midland’s city center.

  • How long is the flight from Midland to Caribbean?

    Airlines like United Airlines, Southwest, and American Airlines fly from Midland to Caribbean in about 7h 36m. The time it takes to get you to your destination can typically vary by up to 9h 28m. The distance from Midland to Caribbean is about 2432 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the most popular routes from Midland to Caribbean?

    The most popular flight routes from Midland to Caribbean are Midland Intl - San Juan Luis Munoz Marin Intl, Midland Intl - Santo Domingo Las Americas and Midland Intl - Montego Bay Sangster Intl.

  • Can I find deals for flights from Midland to Caribbean that include hotel bookings?

    Yes. In addition to deals on Midland to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midland to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midland to Caribbean.

  • Can I find deals for business class flights from Midland to Caribbean?

    Yes. Cheapflights offers flight deals from Midland to Caribbean by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Midland to Caribbean?

    Currently, April is the cheapest month in which you can book a flight from Midland to Caribbean (average of $247). Flying from Midland to Caribbean in July is currently the most expensive (average of $666). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Midland to Caribbean

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Top 3 airlines flying from Midland to Caribbean

Discover the top 3 airlines that operate flights from Midland to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 8, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$307Average$652FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$370Average$558FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$520Average$552FlexibilityNo cancel feeOn-time63%

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